To say that Mitt Romney wants to “have it both ways” is to understate the number of ways in which Mitt Romney wants to have it. Mitt Romney wants multiple overlapping versions of it, with another set parked in an offshore subsidiary, back-dated and post-dated for tax purposes. Having dealt with CEOs and their attorneys for a few years, I find Romney’s approach eerily familiar. Confronted with any sort of financial irregularity, they would tell you that they didn’t do it, or that there was nothing wrong with it, or that it was an isolated or an industry-wide practice (sometimes in the same paragraph) and that anyway they disclaimed any liability three mergers ago. And while you were having this conversation, their lobbyists would have managed to pass a law making whatever they did retroactively legal.

This is all completely, maddeningly legal. And clever people like Mitt Romney can make piles of money in the gaps between the letter and the spirit of the law. But it comes at a cost. Just as Bob Dole and John Kerry had a hard time avoiding the arcane language of the Senate, Mitt Romney does not realize how ridiculous he sounds to 99.5% of the country  when he says he was simultaneously CEO of a company but had nothing to do with it. Or when his spokesman says he “retroactively retired” (the guy who made the Etch-a-Sketch comment is looking pretty good now). To people in Mitt Romney’s orbit, everything is malleable – stock options and pension rights can be back-dated, front-loaded, manipulated in whatever way necessary to ensure that those making the rules maximize their profits.

As best as I can determine, the reason that Romney continued to be listed as CEO of Bain was that the company wanted to practice a very mild form of fraud. While Romney was off saving the Olympics, they wanted to reassure investors that Romney was still in some sense calling the shots. If in fact Romney really was out of the loop, then Bain was engaged in a little deception, but nothing that was legally actionable or even particularly shady by Wall Street standards. This is why Romney gets so genuinely indignant when questioned about this stuff. His behavior was perfectly fine by the standards of his peers. It’s the kind of brilliant flexibility that makes money. But in politics it just makes you Multiple Choice Mitt.

If I were a presidential candidate widely derided for being spineless and telling everyone what they want to hear, you know what I’d do? Go talk to a group that is unlikely to support me anyway and make them boo me.

This post from Josh Marshall has the beginnings of an answer to a question that has genuinely been bothering me. Mitt Romney has been running for president pretty much nonstop since at least 2006. He has a staff of highly paid political operatives. And in all that time, nobody said “Hey, Mitt, maybe you should close those secret bank accounts in the Cayman Islands?” It should be right there on every politician’s checklist, between “quietly resign from whites-only country clubs” and “fire the nanny you’ve been paying under the table.” Particularly if the central theme of your campaign is American exceptionalism.

One answer for this is that Mitt Romney is just a stunningly bad politician. He’s like the opposite of Bill Clinton – I’m not sure he even feels his own pain. I’m not making any moral judgment here, I’m just saying on that critical poll question of “cares about people like you and me” Romney doesn’t even register. All the more reason to pay attention to the cosmetic issues, like parking your money in offshore tax havens. I’m sure it might have increased his tax bills for a few years but good lord he could afford it.

Josh Marshall very wisely suggests the other reason: that Romney and the people around him, including many well-off journalists, just don’t understand how toxic this is. To people at a certain socioeconomic level, moving your money around different banks in different countries is a mundane part of life, no more controversial than shopping for bargains at different outlet malls. To most people outside that circle, banking in the Cayman Islands or Switzerland is something Bond villains do. The weird thing is that Romney is paying vast amounts of money to political consultants who didn’t see this coming. You just can’t get good help these days.